Middlesbrough remain three points shy of the Championship play-offs with three games to go
Tommy Conway scored a 93rd-minute penalty as Middlesbrough maintained their Championships play-off hopes against bottom side Plymouth Argyle.
But Conway's spot-kick, awarded after he was pushed over by Joe Edwards, for which the Argyle captain was sent off, nudges the Devon club closer to relegation.
Miron Muslic's side remain three points adrift of Derby County in 21st but with a far inferior goal difference and only three matches remaining.
For Boro, with Bristol City and Coventry City both winning, the victory was vital as they moved up to seventh, but still three points behind the Sky Blues.
Ex-Argyle loanee Finn Azaz had put Middlesbrough in front early on before Mustapha Bundu equalised five minutes later, and both sides had chances to win it before Conway's 13th goal of the season settled it in Boro's favour.
Argyle had been the brighter in the opening minutes but they showed why they have the worst defensive record in the Championship as they conceded their 83rd goal of the season from Boro's first real attack.
Anfernee Dijksteel's pass opened them up and although Conway's effort came back off the post, Azaz was on hand to put the rebound into the empty net for his first league goal in eight games.
However, a careless piece of defending from Boro meant Plymouth were level within five minutes.
Jonny Howson, on his 750th career appearance, played a loose pass back to Aidan Morris, who had his pocket picked by Bundu, with the Sierra Leone forward finishing confidently past Mark Travers for his eighth goal of the season.
And the bottom club remained the more threatening with Travers saving from Darko Gyabi and then from a one-on-one with Ryan Hardie.
Boro had to improve after the break and Morgan Whittaker, seeking his first goal in his 13th appearance since his January move, nearly found it against his old club but for a fine save from Conor Hazard.
Yet Hardie missed a great chance at the other end when he shot over from 10 yards after more great work from Gyabi.
Conway was denied by Hazard and it looked like they were going to slip further adrift of the play-off places until Boro's top scorer got the wrong side of Edwards running into the area and went down after he was pushed in the back.
Edwards was sent off for a professional foul with Conway sending Hazard the wrong way from the spot to break Argyle hearts.
After the long trip home, Plymouth will have to regroup for the visit of Frank Lampard's Coventry on Easter Monday, with Boro hoping for a favour as they head to Sheffield Wednesday on the same day.
'Late goals are the best' - Carrick
Middlesbrough head coach Michael Carrick told BBC Radio Tees:
"The games are going to flip at times and the picture is going to change quite quickly, but I thought we deserved it.
"We kept going - it's not easy when you have to break teams down all the time. I thought we created enough to score but it's worth the wait. The late ones are the best.
"Great composure from Tommy to take that penalty at the end under the circumstances and it's a big result for us.
"When you get to the end and there's a lot at stake, there are going to be moments and it's whether we can seize them really. Today was for Tommy really."
Plymouth Argyle head coach Miron Muslic told BBC Radio Devon:
"It feels heavy. The lads played a brilliant game.
"Everything we prepared before, we actually delivered. We knew the threat of Middlesbrough - very strong in possession, very strong offensively, but we did it very well and consistently kept our transition threat, creating so many goalscoring opportunities.
"That shows the strong performance we had. And losing this very much deserved point we had with a 93rd-minute penalty, it hurts.
"We have to go again - there is nothing to regret after that 100 minutes. We gave it all."
